Intelligence in the Civil War

Intelligence Collection - The South

For Confederates planning espionage against the North, Washington looked like an ideal site: a city 60 miles south of the Mason-Dixon Line, adjacent to slave-holding states, and full of Southern sympathizers. Many of them were in Congress or in the federal bureaucracy, and had access to valuable intelligence. All recruiters had to do was find among them the men and women who would have the courage and the skill to act as reliable agents.

The earliest known recruiter was Governor John Letcher of Virginia, who laid the foundation for Confederate espionage work in Washington. Virginia seceded from the Union on April 17, 1861, but did not join the Confederacy until May. During the interval, Letcher saw his state as an independent foe of the Union and began his own defense by forming an army and setting up a spy net in his foe’s capital. He knew Washington well: as a member of Congress from 1853 to 1859 and he had been active in the city’s social life.

One of the best-known members of that society was Rose O’Neal Greenhow, a vivacious 44 year-old widow, who partied and dined with Washington’s elite. Openly pro-South, she had wept in the Senate Gallery on January 21, 1861, when Jefferson Davis, one of her many influential friends, said farewell to the Senate and went off to lead the Confederacy.

Letcher got his spy nest started by telling Thomas Jordan, a Virginia-born West Point graduate, to recruit Greenhow. Jordan, who had served in the Seminole Indian War and the Mexican War, was stationed in Washington. Sometime in the spring of 1861, while still a U.S. Army officer, he called on Greenhow and asked her to be an agent. (He soon left Washington and became a lieutenant colonel in the Virginia Provisional Army.)

Greenhow accepted the mission enthusiastically, using her knowledge of Washington’s ways to get intelligence useful for the South. Major William E. Doster, the provost marshal who provided security for Washington, later called her “formidable,” an agent with “masterly skill,” who bestowed on the Confederacy “her knowledge of all the forces which reigned at the Capitol.”

Greenhow’s support of secessionists did not turn away her anti-slavery admirers, who included Senator Henry Wilson of Massachusetts, chairman of the Committee on Military Affairs (and future vice president to President Ulysses S. Grant). Wilson was identified as the author of love letters signed H; one letter said that “spies are put upon me but I will try to elude them tonight and once more have a happy hour in spite of fate.” Another gentleman caller was a member of Wilson’s committee, Senator Joseph Lane of Oregon, who signed his importuning letters to her. Another friend, Colonel Erasmus D. Keyes, General Winfield Scott’s military secretary, later said that she had “tried to persuade me not to take part in the war.”

Jordan instructed Greenhow in a simple, 26-symbol cipher and told her to use his cover name, Thomas John Rayford, for sending him reports. In her memoir about her espionage, she said that she sometimes used a word code. As an example, she told of a letter that said, “Tell Aunt Sally that I have some old shoes for the children, and I wish her to send one down town to take them, and to let me know whether she has found any charitable person to help her take care of them.” What the letter actually meant was: “I have some important information to send across the river, and wish a messenger immediately. Have you any means of getting reliable information?”

The delivery of the ciphered reports to Jordan involved an ever-changing “Secret Line,” the name for the system used to get letters, intelligence reports, and other documents across the Potomac and Rappahannock Rivers and into the hands of Confederate officers and officials. For Greenhow, the Secret Line began with a courier to whom she would entrust her reports. He or she would then hand these off to the next link in the chain of men and women who slipped in and out of taverns, farms, and waterfront docks along routes that connected Baltimore and Washington to the Confederacy.

One of Greenhow’s reports, she later said, had helped the South win the first major battle of the war at Bull Run Creek on the road to Manassas, Virginia, on July 21, 1861.

The Confederate “Secret Line”

The Confederate “Secret Line.”

Modern historians discount her role, attributing the Confederate victory to tactics and errors that produced a Union rout. But P.G.T. Beauregard, the victorious general, gallantly gave her credit for alerting him to the size of the federal force advancing toward Manassas. He said that an enciphered report from her had been delivered to a Confederate picket outpost and quickly passed on to him and on to Jefferson Davis—with an added request for reinforcements.

The carrier of the report was Betty Duvall, a young friend of Greenhow. Duvall, dressed in a farm woman’s clothes and driving a cart, passed through the Union sentinels on the Chain Bridge across the Potomac in Washington, and stopped at a Virginia safe house, where she mounted a horse and rode to the outpost, near Fairfax County Courthouse. She told the officer in charge that she had an urgent message for Beauregard. “Upon my announcing that I would have it faithfully forwarded at once,” the officer later said, “she took out her tucking comb and let fall the longest and most beautiful roll of hair I have ever seen. She took then from the back of her head, where it had been safely tied, a small package, not larger than a silver dollar, sewed up in silk.” Within was the message for Beauregard.

On the advance toward Manassas, the Union troops had overrun the Fairfax outpost and found papers and maps that incriminated Greenhow. Her grand home, not far from the White House, was put under surveillance by Allan Pinkerton, who had been placed in command of the Union Army’s Division of the Potomac after the debacle at Bull Run. “I secured a house in Washington,” Pinkerton later wrote, “and gathered around me a number of resolute, trustworthy men and discreet women.” Pinkerton’s first major assignment was the capture of Rose Greenhow. One rainy night, wanting to peek into her parlor, he went to a high window, removed his boots, and stood on the shoulders of two operatives, “prepared to take notes of what transpired.” A man had entered—and Pinkerton recognized him as an officer assigned to the provost marshal’s office.

“Just at that moment I again received a warning from my supporters, and hastily jumping to the ground, we hid ourselves until the pedestrians had passed out of sight and hearing.” He climbed back on the men’s shoulders and saw the officer show Greenhow a map. The two left the room for more than an hour, returned “arm in arm,” and, with “a whispered good night and something that sounded very much like a kiss,” the officer left.

Rose O’Neal Greenhow and her daughter during her time at the Old Capitol Prison.

Pinkerton followed the officer to a building he did not recognize. Suddenly, four soldiers with fixed bayonets grabbed Pinkerton—and arrested him on the officer’s order. Pinkerton was soon released and the captain arrested. The captain, his career ruined, died sometime later, reportedly a suicide.

A week later, Pinkerton arrested Greenhow at her home and seized documents and personal letters that linked her to Senators Wilson and Lane, along with many other well known Washingtonians. She was charged with “being a spy in the interest of the rebels and furnishing the insurgent generals with important information relative to the movements of the Union forces.”

For ten months, she and several female friends were held in her home. Because she kept attempting to smuggle out messages, she was put in the Old Capitol Prison (now the site of the United States Supreme Court Building). She was released in June 1862 and sent through federal and Confederate lines to Richmond. After Greenhow’s capture, the cipher that Jordan had devised apparently was used for deceptive messages sent by Union officers. Writing about the cipher to Confederate Secretary of War Judah P. Benjamin, Jordan said, “Being my first attempt, and hastily devised, it may be deciphered by any expert, as I found after use of it for a time.”

The Confederates operated at least two other intelligence networks in Washington, both run by cavalrymen and probably set up by the Secret Service Bureau, a clandestine unit within the Confederacy’s Signal Corps. The bureau, a part of the Confederate War Department in Richmond, was commanded by Major William Norris, a former Baltimore lawyer. The Signal Corps ran the army’s semaphore service while the Secret Service Bureau oversaw a communications network whose missions included the running of agents to and from Union territory and the forwarding of messages from Confederate officials in Richmond to contacts in Canada and Europe.

One of the bureau’s most important tasks was the obtaining of open-source material, especially newspapers, from the North, primarily through sympathizers in Maryland, including postmasters. The newspapers provided information—and, occasionally, agents’ messages hidden in personal columns.

The delivery system—sometimes called “our Government route”—boldly relied on the U.S. mail along part of the way. One “mail agent,” a Marylander who lived near Washington, regularly drove his cart there, collected South-bound documents from network members, then hid the mail in manure that he picked up for his garden. Typically, an agent in Union territory wrote a letter, probably in cipher, addressed it to a specific person, such as “Secretary of War, Richmond, Va.,” and placed it in an envelope, which was then sealed and placed inside a second envelope. A U.S. stamp was put on that envelope, which was addressed to a collaborator, usually in Maryland. He or she would then continue the letter on its way by handing it to the first of a relay of mail agents for delivery to “signal camps” in Virginia.

Confederate mail supervisors established several accommodation addresses (as they would be called today) so that a suspiciously large amount of mail did not get delivered to one recipient. The system depended mostly on volunteers, some of whom made the enterprise profitable by adding smuggling to their espionage. There were also riverside farms where Southern sympathizers maintained simple signal systems. One of the signalers was 24-year old Mary Watson, who hung a black dress or shawl from a dormer window to warn boatmen across the river that Union troops were near.

Union officers assigned to investigating the rebel specialdelivery operation occasionally made arrests of mail agents, but the mail kept going through. Major General William T. Sherman was particularly incensed by the regular delivery of northern newspapers. Newspaper correspondents, he fumed, “should be treated as spies…and are worth a hundred thousand men to the enemy.” Yet, like other commanders on both sides, he planted false information in newspapers, well knowing that the enemy would read and perhaps believe the deception.

John S. Mosby

Although the focus of Confederate espionage was initially on Washington, as the war went on, intelligence gathering became more tactical. Distinctions blurred between “spies” and “scouts.” But an age-old custom prevailed: if you were caught in your army’s uniform, you were a prisoner of war; if you were in disguise, you were a spy and could be hanged. Men who rode with the “Gray Ghost,” John S. Mosby, and other such military units were usually considered soldiers.

Many other riders, particularly a Confederate espionage group known as Coleman’s Scouts, were treated as spies.

When Yankee troops captured a group of riders behind Union lines in Tennessee, they singled out one young man who had documents concealed under his saddle and in his clothing. Besides information about federal defenses in Nashville, the man, Sam Davis, had a piece of paper signed E. Coleman.

Union interrogators, seeking information on the notorious Coleman’s Scouts, focused their attention on Davis. He knew that “Coleman” was the cover name of Captain H. B. Shaw, who had also been captured and was being held in a nearby cell. But when Brigadier General Grenville M. Dodge, a Union intelligence officer, demanded to know who and where Coleman was, Davis refused to talk. He remained silent even when Dodge threatened to hang him.

Davis, a 21-year-old infantryman, was a courier for Shaw. When he was hanged on November 27, 1863, he went into Confederate legend not as a courier, but as a spy. The legend has him say, “I would sooner die a thousand deaths than betray a friend or be false to duty.” He became “the South’s Nathan Hale,” one of many captives executed as spies by both sides. The number of suspected spies executed by both sides is not known because of the lack of records and the secrecy that surrounded most executions.

Because “spies” and “scouts” were used interchangeably, it is difficult to sort out “espionage,” which is the work of spies, from “reconnaissance,” which is the work of trained observers, such as cavalry scouts. Confederate General Robert E. Lee, for example, received a steady stream of intelligence from what would be called agents or spies today. In a report to Confederacy President Jefferson Davis, Lee said that “our scouts on the Potomac” had learned that a Union army was about to march because “three days’ rations had been cooked and placed in the haversacks of the men.” Another so-called Southern scout seemed more likely to be a spy because he “was able to converse with” Union troops to get an accurate estimate of the size of a deployment.

Lee’s greatest scout, Major General Jeb Stuart, won public fame as a dashing cavalryman leading audacious raids behind Union lines. But when he was killed in action in 1864, Lee gave him an epitaph worthy of a great spy: “He never brought me a piece of false information.”

The Flamboyant Spy

Jeb Stuart

James Ewell Brown Stuart, better known as Jeb Stuart, was the grandson of a Revolutionary War hero and son of an Army officer who served in the War of 1812. Jeb Stuart was born in the family homestead in Patrick County, Virginia, on February 6, 1833. After attending Emory and Henry College, he entered the U.S. Military Academy, graduating in 1854. Three years later, as a cavalry officer in the West, he was wounded in an Indian battle.

While on duty in the Kansas Territory, Stuart pursued an abolitionist known as Ossawatomie Brown, who was accused of illegally freeing slaves. On October 17, 1859, Stuart and Brown would cross paths again. Stuart accompanied Lieutenant Colonel Robert E. Lee, who led a U.S. Marine force to Harpers Ferry to fight raiders who had seized the federal arsenal and rifle factory there. John Brown, who called himself Isaac Smith, had barricaded himself and his followers in the armory fire engine house. Lee sent Stuart to the door with a white flag. The man known as Smith “opened the door about four inches, and placed his body against the crack, with a carbine in his hand,” Stuart later wrote. “Hence his remark after his capture that he could have wiped me out like a mosquito. When Smith first came to the door, I recognized old Ossawatomie Brown who had given us so much trouble in Kansas.” Later, Stuart searched Brown’s lodgings and found documents that disclosed details of Brown’s plans for leading a slave revolt. This was Stuart’s first venture into the gathering of intelligence.

When the Civil War began, Stuart resigned his U.S. Army commission and joined the Confederacy. He rose rapidly, becoming a brigadier general in 1861 and in 1862, as a major general, chief of cavalry of the Army of Northern Virginia. He seemed too flamboyant to be a spy. “He could wear, without exciting a suspicion of unfitness, all the warlike adornments of an old-time cavalier,” a biographer wrote of Stuart. “His black plume, and hat caught up with a golden star, seemed the proper frame for a knightly face....”At a time when scout and spy were often used interchangeably, Stuart’s military exploits eclipsed his espionage at least in public. But Stuart’s espionage was well-known by General Robert E. Lee, who took a personal interest in the covert work of Stuart’s scouts. One of them, Lee wrote, “sometimes acted under my special direction.”

One of Stuart’s scouts, Benjamin Franklin Stringfellow, became an extraordinarily competent agent. For a time, Stringfellow posed as a dentist’s assistant in Union-occupied Alexandria, Virginia, while regularly sending reports of Union troop movements. Later, he used the same cover while an agent in Washington, where he even got a dental license.

Stuart, who had trained Stringfellow, said of him, “In determining the enemy’s real design, I rely upon you, as well as the quick transmission of the information.” Stringfellow’s information, Stuart said, “may be worth all the Yankee trains” that Stuart attacked. Stuart’s colorful career ended on May 11, 1864, when he was fatally wounded while defending Richmond. When Lee learned of Stuart’s death, he said, “I can scarcely think of him without weeping.”